Thanks — I can help. That login loop is usually caused by a credentials/token problem (the little Microsoft web-auth window fails to complete), or by the account you’re using not being available/eligible in the context the enrollment dialog expects. Let’s troubleshoot step‑by‑step.
Quick questions before we dive in
- Which Windows version and edition are you running? (Press Win+R → type winver → Enter, then post the window text or a screenshot.)
- Is the account you’re signing in with a personal Microsoft account (example@outlook.com / @hotmail.com) or a work/school (Azure AD / Office 365) account?
- Is the PC joined to a domain or to Azure AD, or is it a local-only machine?
- Do you use MFA (Authenticator app, phone, or SMS) on that Microsoft account?
Try these steps (do them in order) and tell me which step changes anything or what error you see.
1) Look for a hidden sign‑in window
- After clicking “Sign into your account”, press Alt+Tab to see if a small authentication window opened behind the ESU dialog. If found, complete the prompt (MFA approval, etc.). Sometimes WebView dialogs appear behind full-screen dialogs.
2) Confirm Windows version & signed-in account
- Run Win+R → winver and paste the result here.
- Open Settings → Accounts → Your info and Settings → Accounts → Email & accounts and check whether your Microsoft account is listed under “Your info” or “Accounts used by other apps”. If it is listed, tell me whether it shows as “Connected” or shows an error.
3) Sign into account.microsoft.com in a browser
- Open Edge or Chrome, go to https://account.microsoft.com and sign in with the same account. Confirm you can sign in there and complete any MFA prompts. If a prompt/approval appears, do it. If this fails, fix the account sign-in first (Microsoft site will show the actual error).
4) Remove cached Microsoft credentials (safe)
- Open Control Panel → Credential Manager → Windows Credentials and Web Credentials.
- Remove any entries that reference microsoftaccount, microsoft, live, or the email address you’re using.
- Restart the PC and try the enrollment again.
5) Reset Microsoft Store & Web token components (common fix)
- Open an elevated (admin) PowerShell and run:
- wsreset.exe
- Then run:
Get-AppxPackage -allusers Microsoft.WindowsStore | Foreach {Add-AppxPackage -DisableDevelopmentMode -Register "$($_.InstallLocation)\AppXManifest.xml"}
- Restart and try the enrollment again.
6) Re-add the Microsoft account to Windows
- Settings → Accounts → Email & accounts → Add an account → sign in with your Microsoft account.
- If the account is already present, remove it (select it → Remove) then add it again.
- After re-adding, retry the ESU enrollment.
7) Try from a different local admin user
- Create a new local administrator account (Settings → Accounts → Family & other users → Add someone else to this PC → I don’t have this person’s sign-in info → Add a user without a Microsoft account → make it an Administrator).
- Sign out, sign into that new account, then add your Microsoft account there (Settings → Email & accounts) and try the enrollment from that account. This isolates profile-level issues.
8) Check time/date & network/proxy
- Make sure system date/time are correct (Settings → Time & Language). A wrong clock breaks Microsoft auth tokens.
- If you use a VPN or proxy, temporarily disable it and try again.
9) Look for an error in Event Viewer (if above doesn’t work)
- Open Event Viewer → Applications and Services Logs → Microsoft → Windows → Account/Identity (or look in Windows Logs → Application) around the time you click Retry. If you see an error, copy the event ID and the full error message here (or a screenshot).
10) If this enrollment requires a purchased ESU license
- Ensure the account you’re signing into is the one that has the ESU purchase/eligibility. Some ESU enrollments require an Azure / Volume Licensing identity or a specific account the purchase was made with. If you don’t have that, the dialog may sign in but not proceed.
What I suspect (and why)
- Most often this is a cached token / WebAuth WebView problem (steps 4–6 fix this).
- If the account is a work/school account or the device is domain/Azure‑joined, there may be a policy or an eligibility requirement that blocks completion (step 10).
If the above doesn’t fix it
- Post the WinVer text and tell me whether the account is personal vs work/school and whether you saw any MFA prompts when signing into account.microsoft.com.
- If you can, attach a screenshot of Settings → Accounts → Email & accounts (so I can see if the account shows any error text).
- I’ll then give the next detailed commands and, if needed, the exact Event Viewer queries to capture the auth error.
Don’t share passwords here. Follow the steps and tell me what you see at each stage and I’ll guide the next action.
